Acetic Anhydride → HCID 12838038, compound

HRID 1447113Notes

Reaction equation

HRID 1447113 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][NH:10][CH2:9][CH2:8]2.[C:13]([O-])(=[O:15])[CH3:14].[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:13]([N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([Cl:2])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 125950728-Chloro-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 12838038HCID 12838038, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 20.4 g. (0.1 mole) 8-chloro-1,2,3,4-tetrahydroisoquinoline, hydrochloride, 9.85 g. (0.12 mole) sodium acetate 40 ml. acetic anhydride and 100 ml. acetic acid was heated for 3 hours on a steambath with stirring. After the solvent was removed under reduced pressure, the residue was dissolved in water which was then made basic with concentrated ammonium hydroxide. The crude product was extracted into methylene chloride and the organic solution was washed with water, 10% hydrochloric acid, water and 5% aqueous sodium bicarbonate. The organic solution was then dried over anhydrous magnesium sulfate and then concentrated to dryness under vacuum to afford 2-acetyl-8-chloro-1,2,3,4-tetrahydroisoquinoline as a yellow oil.

Workup

  1. additionA mixture of 20.4 g
  2. customAfter the solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water which
  4. extractionThe crude product was extracted into methylene chloride
  5. washthe organic solution was washed with water, 10% hydrochloric acid, water and 5% aqueous sodium bicarbonate
  6. dry with materialThe organic solution was then dried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-f382f2d0f52648e1a116ec4774f6ae3b
Source dataset
uspto-grants-1982_02
Patent number
US04315935

Reaction notes

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